


First and Last

by Piper_Halliwell1979



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Apologies, Arguing, Banter, Bottom Castiel, Case Fic, Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester First Time, Coming Out, Developing Relationship, Fake/Pretend Relationship, First Kiss, First Time Blow Jobs, First Time Bottoming, Flavored Lube, Gay Crush, Innuendo, Jealous Castiel, Love Confessions, M/M, Miscommunication, Past Relationship(s), Pet Names, Safer Sex, Season/Series 13, Separate Rooms, Supportive Sam Winchester, Talking, Teen Romance, Telling Sam, bossy bottom, brothers talking
Language: English
Status: Completed
Published: 2018-03-29
Updated: 2018-03-29
Packaged: 2019-04-14 17:22:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 7,733
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14140836
Author URL: https://archiveofourown.org/users/Piper_Halliwell1979/pseuds/Piper_Halliwell1979
Summary: A glimpse into Dean's past exposes a secret that may open up new possibilites for the future.





	First and Last

Dean had been encouraged by Sonny to go out for the school’s wrestling team. He had some moves, having been following wrestling on television and John taking them to a handful of live matches. At least he thought he did. The first day after school he found himself flat on the mat more times than he could count. He was embarrassed and frustrated. 

  


A hand extended down to help him up. “You’re quick. Think on your feet. You just gotta learn the regulation moves. You’re Dean, right? I’m Connie. Well, Conrad but I hate it.”

  


“Thanks. I dunno why I bothered. Just looking for something to do besides chores after school,” Dean tried to shrug his failure off. Conrad... _ Connie _ nudged his shoulder and grinned. 

  


“Come in before first period. I’ll show you a few moves you can throw back at me at practice.”

  


It was an excuse to be out of the boys’ home. “Sure. Yeah. See ya at ass o’clock.” Dean went to change back into his street clothes. He was halfway to the elementary school when he remembered he didn’t have Sammy to look after.

  


The next morning he showed up and changed into sweats for his wrestling lesson. Connie was waiting for him with some mats on the gym floor. “Heard you were one of Sonny’s kids.”

  


“Shit. Look. If you wanted to kick my ass, you’re in for a surprise,” Dean squared up.

  


“Dude, chill. Was just gonna ask what you did.”

  


“Shoplifting. My old man went out of town on a job and it went longer than the money he left for food. Cops sent me to Sonny’s till he gets back. Nothing exotic. And I ain’t no psycho. Dad was a Marine. Taught me to fight.”

  


Connie just smiled at him. “Okay. Not a future serial killer. Ready to hit the mat?”

  


Dean managed to pin him twice in the hour they spent together that morning. After school he did much better against the other guys. He got the attention of the coach, who told him he had a chance of making the team at the end of the week. Connie offered to take him out for a burger and a shake to celebrate. Dean would never turn down a free meal. He called Sonny from the payphone at the diner to let him know where he was.

  


Connie was cool. They liked the same kind of movies and music. They talked about how awesome Dean’s father’s car was and how Dean hoped to inherit it one day. The Impala would be his baby. He let Connie walk him back towards Sonny’s and they agreed to meet before school the rest of the week.

  


Dean made the final cut. Sonny came to cheer him on for his first match. He and Connie spent a lot of time together and it was nice. Connie didn’t judge him for having a less than reliable father. His friendship made things easier on Dean for being the new kid and the foster kid. Sonny thought him making real friends was good for him and gave him a little slack with chores. He had something else to keep him out of trouble.

  


Then Connie reached across the seat of his truck for Dean’s knee after dinner one day. His heart was racing and he was confused. What was he supposed to do? “Connie?”

  


“Dean, I thought I was picking up a vibe from you. It’s a cheesy move but...look, if I’m wrong...tell me to move my hand and there’s no hard feelings. Small town. Hard to meet people.”

  


Dean gulped. Okay maybe he thought Connie was a good looking guy. Maybe he looked at his lips a few times and wondered...maybe…”Nah. It’s okay. I just...nobody’s ever made a move before.” He tentatively put his clammy hand over Connie’s. He was still tense. Any minute Connie could laugh at him and call him a ‘fag’ or something before he called all his wrestling buddies to out him.

  


Connie pulled the truck over near Sonny’s. “Would it be okay to kiss you?” he asked.

  


Dean’s stomach was in knots. He might act like a player but the truth was he hadn’t been around any girls long enough to work up the nerve for a kiss. He just nodded and let Connie come to him. In the back of his mind he was ready to get socked in the jaw but was surprised by the warmth of soft lips on his.

  


It was nice. Even the butterflies in his stomach. His fifteen year old dick twitched in his jeans. He let Connie deepen the kiss as he fought his internal panic button. There was no John. There was no Sammy or Uncle Bobby or Pastor Jim. It was just him being liked by somebody and it felt good.

  


When Connie broke away he was all smiles. “I like you, Dean. But please don’t think I’m an asshole for this. We gotta keep this on the down low.”

  


“Yeah. I understand,” Dean agreed. “I like you, too.”

  


“Good. Umm...if Sonny’s cool with it, you wanna go to a movie after practice? Like a date?”

  


“A date? Won’t Sarah ask why you’re taking me instead of her? I noticed Fridays are kind of when everybody hangs out.”

  


Connie laughed. “Sarah has a girlfriend she met at camp last summer. She knows about me. We look out for each other. Keep each other off the radar. You should probably make a girl friend, too. Just for dances and stuff.”

  


Oh. Dean hadn’t thought about that. He’d already been in one place longer than he expected to be. “There’s this girl that comes to give guitar lessons. Robin. I could try to get her to come with for when everybody goes out.”

  


“Then tomorrow night it’s just me and you and then you could maybe invite her to come bowling Tuesday. It’ll be a bunch of us.”

  


“Yeah. Okay. I’d like that.” Dean leaned over for one last peck before getting out and heading back to the house.

  


Robin was not falling for any of his silly attempts. It took a lot of work just to get her to think about him as more than a mysterious bad boy on the farm. When she kissed him, everything got confusing for him again. He thought maybe he was gay since he liked making out with Connie. But Robin was just as nice and he started liking her, too. He asked her to the dance, hoping he had the balls to call things off with Connie and act ‘normal’. He never got the chance to say goodbye to either of him. Seeing his baby brother playing in the back seat of the car pulled all his heartstrings back to Sammy. 

  


He rode away with John after collecting his few belongings and a tearful goodbye with Sonny. At least when he slipped about something he did with Connie his father and brother assumed he meant a girl. He never bothered correcting them. He wrote Connie off as curiosity, an experiment. Any pangs he felt towards the male persuasion after that he chalked up to missing that part of his life and not a sexual identity crisis. For all Sam knew, his first kiss was with a  _ girl _ named Connie. And then his second was a girl named Robin a couple weeks later. He kept up the charade that he was a ladies’ man.

  


Dean was relieved that Connie hadn’t stuck around when he and Sam came back to work a case for Sonny. Robin acted like she didn’t remember him at first but the bad blood had its way of coming to the surface. After all those years he still felt like a dick for standing her up. He wondered if she’d heard rumors of his brief affair with Connie after he left but if she didn’t bring it up he sure as hell wouldn’t. Sam didn’t ask him about Connie either. One more day with his secret safely compartmentalized.

  


***

  


“Man, I hate these school gigs. Either something hurting kids or a vengeful spirit of a kid pushed too far.” Dean adjusted the tie of his suit and pocketed a fake badge. He made sure Cas’ badge was facing up and gave him a last minute primp as well.

  


“You could have gone to the sheriff’s office instead, Dean,” Cas countered.

  


“Yeah. But this way you get to hang with me,” Dean smiled and patted Cas’ shoulder. “Come on, flex your ‘people skills’ muscles.” They asked a passing student for directions to the office so they could question the principal first. Dean’s entire body tensed when he saw the nameplate on the door. 

  


Cas must have sensed it because he placed his hand on Dean’s shoulder to help ground him. “We can step out if you need a moment.”

  


Dean shook his head. “I know this guy, Cas. Or...I did. Long time ago. Probably won’t remember me.” He knocked on the door and waited for the invite to come in. 

  


He was a couple decades older but still a handsome guy. Connie’s eyes widened like he’d seen a ghost before his lips parted into a smile. “I’ll be damned. Dean Winchester. I don’t remember the district posting a position for a new wrestling coach.” He stood and reached for Dean’s hand. Dean noticed the gold band.

  


“Married?” He asked over the huge lump in his throat.

  


“Uh...yeah. Well, legally a couple years ago but we’ve been together since college. Is this your…” Connie gestured towards Cas.

  


“Partner,” Cas was quick to answer. Dean gritted his teeth. Cas had no idea he just told an openly gay man that he was Dean’s significant other. 

  


Dean flicked a quick glance at Cas before taking his hand. “Going on ten years. So...uh…” he searched for an excuse for them to be there. “We might be relocating to the area and our son, Jack, he's sixteen. Looking at schools and whatnot before the final decision. Then we read about some weird sh..stuff going on.”

  


Connie gestured for them to sit. “It’s horrible. Losing a student under any circumstance affects the entire community. Usually it’s a car accident or suicide. But...murder? Ashley Miller was a great kid. She was smart and outgoing. Student council. I assure you this is an isolated incident and that the police are investigating the matter.”

  


Cas looked to Dean first and accepted the tiniest of nods as permission to continue with their new undercover story. “Our concerns for our son’s safety are a priority. How can you be certain this was an ‘isolated incident’?”

  


“I don’t want to get into the more gruesome details, but the suspect is someone somewhat transient. They arrived and left on a vintage motorcycle. It appeared to be a random act of violence.” Connie carefully explained. It was essentially what the police were about to disperse to the media.

  


Dean had his suspicions. “How about a drastic change of subject, huh?” He flashed his best fake smile. “Tell me about clubs...activities...diversity?”

  


“Diversity. Well, the school board has no issues with an openly gay man as the high school principal. Your son would have no issues as the child of a same sex couple. There are acceptance clubs as well as the standard chess, archery, debate, faith…”

  


“Faith? Like exclusively Judeo-Christian?” Dean cut him off.

  


Connie shook his head. “There are many faiths represented. There’s even Pagan and Atheist clubs.”

  


“Good. Um...we’re agnostic but Jack seems to have taken an interest in Wicca so we support that. We want him to be in an environment where he can be himself.” Dean fished for confirmation of some teen witches or wannabes. If there was a coven, Ashley Miller was likely the real deal. And she’d fallen to the same fate Ketch had left others before her.

  


“Are you going to be in town long? Maybe bring your son to the game this weekend if that’s his thing. Does he know his old man was somewhat of a wrestling star back in high school?” 

  


“Was this when you were at Sonny’s, Dean?” Cas squinted his eyes at him. “I apologize. I just made the connection. You’re  _ Connie _ . He has spoken fondly of you.” The squint turned slightly accusatory.

  


The principal blushed. “This shouldn’t be this awkward after twenty five years. Mr…”

  


“Winchester. Cas Winchester.”

  


“Mr. Win-Cas, Dean and I were both a couple kids figuring out who we were. Your son is at that age now.”

  


Castiel put up a hand. “I didn’t intend to make this awkward. My... _ husband _ only mentioned being familiar with your name. I didn’t realize I’d be meeting someone significant from his past without even a proper introduction.”

  


Dean felt like an asshole. “Cas, I’m sorry. I wasn’t even sure it was the same guy until we stepped into the office. It’s supposed to be about Jack. We can talk about all this later,  _ honey _ . Please.”

  


Connie turned around to get some things out of a file cabinet. “How about I give you the prospective student packet and enrollment forms if you decide this is the place for your son? You can have him look it over and even schedule a meeting for him with me to ask any questions  _ he _ might have.” 

  


Dean took that as a cue for them to leave before Cas got all smitey. He had a  _ lot  _ of explaining to do and he knew he’d have to come clean with Sam later. “Thanks, Connie. It was nice to see you again. Or are you going by Conrad? Sorry.”

  


“Still Connie. Nice to see you as well. And to meet your husband, Cas. I hope to hear from you soon about your son enrolling.”

  


Dean kept his arm around Cas’ waist until they were back to the Impala. Cas slammed the passenger door when he got in. “Alright, Cas. Get it all out. I deserve it.” Dean braced himself.

  


Cas started by pinching the bridge of his nose. “I’m angry that you thought so little of me that you wouldn’t confide in me. I’m angry that you obviously have been suppressing a part of yourself that deserves to be an open aspect of you. And I’m angry that you can only ‘pretend’ to be involved with me when all this time it’s actually been attainable.” Cas loosened his tie. “I won’t tell Sam if you don’t want me to.”

  


There it was. All the guilt tying his stomach in knots. “I’m gonna tell Sam about Connie. He should know. You both should've. I...it happened when I was really confused about stuff. I almost stayed at Sonny’s to give up hunting. I kissed a boy and a girl within a couple weeks and I liked them both. I wanted to be ‘normal’ and at the time I thought it meant stick with girls. I know better  _ now _ . And this has everything to do with my own insecurities. I do trust you, Cas. I just wasn’t ready.”

  


Cas reached over and placed his hand on Dean’s thigh. “Are you uncomfortable with a man touching you?” he asked.

  


Dean’s mind flashed back to when Connie made the first move. He was nearly as nervous now. “No. I’m not.” He put his hand over Cas’. “What did you mean by ‘attainable’?”

  


“That if I suggested a romantic relationship with you...it would be plausible for you to be amenable.”

  


Oh. “Oh? Is that something you’ve really thought about?” Dean tested the waters.

  


“As an angel and as a human. Had you let me stay in the bunker after I fell...I likely would have confessed the feelings I’d begun to understand. But when you call me things like ‘brother’ and ‘family’ I take it to mean it would be a fruitless endeavor.”

  


Fuck. He’d friend-zoned Cas. The Cas he actually wanted in his personal space. The Cas whose lips he’d dropped his eyes to during nearly every conversation. The Cas who made him constantly re-evaluate where he landed on the Kinsey scale. “I dunno what I would have said then. Probably would have given you a million reasons why you shouldn't want me.”

  


“And now? If I asked you to kiss me?” Cas looked at him with hopeful eyes.

  


“Now,” Dean took in a deep breath, “I’d probably kiss you.” He leaned over to meet Cas in the middle of the front seat. He kissed the angel softly and chastely, just pressing their lips together for a few seconds. “Was that okay?”

  


“Very. Please do it again.” Cas closed his eyes and left his lips slightly parted. Dean kissed him deeper that time, curling his hand around the back of Cas’ neck. Cas’ tongue brushed against his and it felt just as right and as exhilarating as Dean’s first kiss.

  


Dean broke it off and cleared his throat. “Um...much as I’d like to uh...you know, keep doing this...we gotta meet up with Sam.”

  


“I understand, Dean. We need to find Ketch. Or warn the other witches of the danger they’re in. I’d like to continue this later. Privately.”

  


“Yeah. Me too. I’ll get us a separate room. We can... _ talk _ about stuff.” Dean gave him a quick peck and smiled at him. “After I come clean with Sam.”

  


“You don't have to…”

  


“I do. You don’t wanna sneak around behind his back, do ya?  _ I _ don’t. Me and him are finally in a good place.”

  


“Okay.” Cas moved back to his place in the passenger seat. Dean called Sam for a meetup for lunch to compare notes. They waited for him on the same side of the booth.

  


“The sheriff gave me what she had. Told her we may be looking at an interstate serial killer. Poor girl was nearly decapitated when she got her throat cut. Witnesses are pointing to a drifter on a classic motorcycle,” Sam started. “How’d it go at the school?”

  


“She was involved in a Wicca group. May have been the real deal. Who do we know on a bike who’s been icing witches?” Dean answered.

  


“Ketch. So now what? He’s already onto the next target. No closure for Ashley’s family.” Sam looked over the menu.

  


“Well, me and Cas have a pretty good cover story. You find us schools with those kinds of extracurricular activities and we go in as prospective parents looking for the ideal school to enroll our son Jack.”

  


Sam scoffed. “You ditched your badges to be gay dads? Not exactly your style, Dean. Smart, though,” he added.

  


Dean glanced at Cas. “Turns out I know the principal. We kind of had a... _ thing _ back in the day. If he wasn’t out he’d at least have an open mind. Turns out he married his college boyfriend.”

  


Sam’s eyebrows went up. “You and him had a  _ thing?  _ When was this?”

  


“When I was at Sonny's, okay? He’s Connie. It was a nickname for Conrad. So...he was my first kiss.” Dean watched his brother carefully for his reaction.

  


“Huh. You could have told me, Dean. Wouldn’t have changed anything.” Sam went back to reading. When the waitress showed up he settled on a grilled chicken sandwich and side salad. “Did you know, Cas? Your whole bond thing?”

  


“I was not made aware until this afternoon, Sam. It was a rather enlightening revelation. Dean and I have agreed to discuss it further later. In a separate motel room,” Cas responded.

  


Sam smirked before chuckling to himself. “Yeah. You guys should definitely  _ talk _ .”

  


“What’s that supposed to mean?” Dean balked.

  


“Does the phrase ‘sexual tension’ mean anything to you? I swear some of the looks you give each other should come with a parental advisory. Just get your room on the other end of the motel and I’ll start looking into the school thing. Quietly. Alone.”

  


Dean opened his mouth to speak but the burger placed in front of him took precedence. He eyed the second burger on Cas’ plate. “Might wanna eat that. Keep your strength up.”

  


“Dean, I don’t require... _ oh. _ ” Cas popped a couple fries in his mouth. Sam squirmed across from them.

  


“Okay. Let’s no longer be so candid about our sexual conquests. We’re all adults. We’re all healthy, active people. I’m cool with getting two rooms from now on and if you two get all cute and lovey-dovey I reserve the right as the younger brother to tease you relentlessly,” Sam proposed. 

  


“Lovey-dovey, huh? So, Cas...do you prefer shnookums or hunny-bunny? Pumpkin? Cupcake?” Dean teased. Cas glared. “Come on, pet names?”

  


“I thought your nickname for me was ‘Cas’.” he said dryly. “You balked when I tried to call you ‘honey’ once.”

  


“Well...honey is a good pet name. Babe is another. Sweetheart…”

  


“I liked it when you called me Sunshine. It felt like being referred to as light and life.”

  


Sam broke into a giggling fit. “I  _ love _ this! You called Cas the light of your life! Bickering over what terms of endearment to use. I can’t tell if you’re newlyweds or an old married couple.”

  


Dean put down his burger and motioned for the waitress. “Can I get the check and a couple boxes? Me and the missus gotta split.”

  


“Dean, you will  _ not _ effeminate me,” Cas warned too low for her to overhear.

  


“I’m just kidding, babe. Anybody can see what a hot guy I landed.” Dean pulled a couple twenties from his wallet. “Keep the change, Becca. Big guy's is on me.”

  


She smiled just the same as she did to all her customers and brought back two styrofoam containers for Dean and Cas. He loaded them up and gave his brother a mock salute before exiting. 

  


“You’re still mad,” Dean deduced when Cas kept the tension in his shoulders. “It was a joke. Apparently a very stupid one. I thought I was being cute and pestering Sam. I wasn’t trying to  _ effeminate  _ you.”

  


Cas seemed to accept that. “You aren’t the only one processing the change in the nature of our relationship. I don’t see you any differently. Your attraction to men has always been a part of you. It’s always been a part of the man I care for. If you care for me the same then treat me the same.”

  


Dean took his hand. “Deal. And if you’re really not cool with the pet names we don’t have to do that either. It’s...couple stuff. I’ve only been in one serious relationship. I dunno what I’m doing.”

  


“I don’t either,” Cas admitted. “Just what I’ve seen from the films we’ve watched together. I don’t believe either of us are a prostitute or business executive…”

  


“Yeah, yeah.  _ Pretty Woman _ . We’ll figure it out as we go. Just like everything else we do. I’ve kissed a total of  _ two _ guys. I’ve held hands with two guys. Anything beyond that is a whole new world.”

  


“ _ Aladdin.” _

  


Dean grinned. “Okay, you know your movie quotes. Let’s go finish our burgers in peace.” He started up Baby and headed for the motel. 

  


***

  


“Dean? Could we kiss again?” Cas asked after they’d settled into their room. Dean had them take off their shoes and socks and outer layers. They stuffed the leftovers in the mini fridge and found something on the television for background noise. They were both lying on the bed, nervous about the possibilities. Cas rolled to his side and Dean moved to face him. 

  


The kiss was soft. Dean knew they could do that comfortably. He was good at kissing and apparently so was Cas. He definitely learned a thing or two from the pizza man. They eased into the longer and deeper kisses, moving closer to each other so they fell into an embrace. At some point Dean found himself on his back with Cas on top of him. 

  


“Cas...Cas...hold up a second,” Dean panted. He knew he was getting into it and felt Cas firming up too. “Do you know what you’re doing?”

  


“No. But it feels good.”

  


“It does. Shit. I didn’t think this through. I mean...there’s  _ stuff _ we can do. But I don’t have stuff for... _ other stuff _ .”

  


“You aren’t making sense, Dean.”

  


Dean huffed his frustration. All the bloodflow was heading the opposite direction of his brain. “Sex, Cas. It’s not like sex with a woman. I mean, condoms I got. But guys need lube or it’s gonna be really uncomfortable.”

  


“Then we don’t have penetrative sex. We can do the other things you suggested. If you want. I’m content with kissing you and the...friction.” Cas looked down between them.

  


“I want. Believe me, I want. Um...you’ve jerked off before, right? When you were human? Dealt with morning wood?”

  


Cas blushed a little. “I did. It seemed a biological necessity.”

  


“Then we’ll ditch the pants and do that. But...for each other.”

  


“That was also more pleasant with proper lubrication.”

  


Dean sighed. “You’re right about that. Maybe the universe is telling us something here. Maybe we’re pushing this to happen too soon.” 

  


Cas sat back on Dean’s legs. “I’ve seen you leave a bar ten minutes after arriving with a woman. I’ve waited ten years for you.”

  


Dean sat up a little too. “That’s just it, Cas. You’re not some random hookup. You’ll still be here in the morning and every morning after that. I want this, Cas. God, I’ve wanted you for so damn long. So maybe it means more to me that we do this right. You’re special. You deserve our first time together to be more than some sweaty grunting on a cheap mattress.”

  


Cas looked like he might cry. “I love you, you know. I may not hear those words back from you...but what you just said felt pretty damn close. I  _ do _ want a perfect night with you. It doesn’t matter to me if it’s in a motel or at home in your bed. What matters is how you feel when you touch me.”

  


“So…?”

  


“So give me the keys, Dean. I’m going to the pharmacy to get what we’ll need. When I come back we’ll watch a movie and talk and kiss and if it happens...it happens. If it doesn’t I’ll hold you and watch over you tonight and every night until it does.”

  


Dean gently cupped Cas’ face. “I do. Even if I can’t say it. I do.” Cas leaned forward to kiss him. “Keys are on the desk.  _ Sunshine. _ ”

  


“I’ll be back.”

  


***

  


Dean did what any twitterpated man would do. He called his best friend. Who also happened to be his brother.

  


_ “This better not be a butt dial where all I hear is moaning and heavy breathing.” _

  


“No. He’s not here. He went out to pick up a few things.”

  


_ “So you guys haven’t…?” _

  


“No. I’m nervous, man. I’ve never done this. You know, with a guy.”

  


_ “You haven’t? Wow. I thought you and Crowley…” _

  


“Whoa, whoa...no. We might have participated in  _ group  _ activities but there was no crossing streams.”

  


_ “Still very disturbing. So why are you calling me?” _

  


“Because this is big, Sammy.”

  


_ “Did not need to know that. Use lots of lube?” _

  


“Damnit. What I meant was...once I go there with Cas, there’s no going back. He’s probably it for me. Things are gonna change and me and him will be an  _ us _ and I need to know if you’re okay with that.”

  


_ “Of course I am, Dean. Cas is my best friend but he’s always been something more to you. Even in the beginning. If you’re looking for my blessing or whatever, you have it. Just don’t do or say stupid shit to hurt each other.” _

  


“Thanks, Sammy. Um...any advice?”

  


_ “I’ve never had sex with a guy either, asshole. Haven’t you seen enough porn to know what you’re doing?” _

  


“That’s  _ porn _ ! I actually had sex with a porn star and it wasn’t like her films.”

  


_ “I can’t believe I’m saying this...top or bottom?” _

  


“Fuck. I guess the opposite of what he picks?”

  


_ “Well, that’s your first obstacle. Take your time. Make sure whoever is on the receiving end is relaxed and comfortable. And be safe.” _

  


“Relaxed. Got it. Hope he brings back a bottle of hooch.”

  


_ “Dean, it sounds like you’re not ready. It’s okay to wait. You don’t have to consummate your relationship to prove anything. Just acknowledge him as your partner. Or boyfriend. Whatever you wanna call it. There’s other ways to show your commitment than sex.” _

  


“I know. But he said he’s waited ten years for me. How much longer do I have to make the guy wait?”

  


_ “Until you’re ready. Cas is a good guy. He’ll understand. And if he doesn’t I’ll kick his ass. Okay?” _

  


“Okay. Thanks for talking me through this. Promise I won’t scar you for life with any details.”

  


_ “That’s all I ask, Dean.” _

  


He still felt just and nervous and confused after his chat with Sam so he got out his laptop. He expected his search to lead right to porn but instead he found a couple articles about safe anal sex. What he read actually wasn’t that scary. Hell, even straight dudes liked a little backdoor action. Reading about intense prostate orgasms sounded like a great time. He slammed the laptop shut when he heard Cas’ key in the door.

  


“Were you watching porn?” Cas asked.

  


“No. I was actually doing some research. About gay sex. But not porn.”

  


Cas kicked off his shoes again and brought the plastic bag from Walgreens with him to show Dean his purchases. “I didn’t realize there were so many options. I have cherry flavored lubricant for oral sex. Water based lubricant for mutual masturbation and anal sex. And silicone based for shower sex. At least that’s what Keith at the pharmacy explained. Also, Magnum condoms. I rebuilt you. I am fully aware of how well endowed you are. I also have a large penis.”

  


Dean looked everything over. “Some dude named Keith helped you with all this? What the hell did you say to him?”

  


“He found me reading all the boxes and asked what I was looking for. I...sarcastically said midlife crisis sex with my new boyfriend. He was very helpful.”

  


Dean grinned. “Midlife crisis sex. Awesome. At least we’re prepared and responsible. And  _ I _ have a much better idea on how we go about doing that. But I still wanna just chill here in bed for a little while. We can ditch the pants and keep on our boxers, though. I read the key is relaxation.”

  


Cas seemed amenable to that. He stripped down to his expose not boxers, but bright orange boyshorts. His junk made a very noticeable bulge in the front. They clung to his perfect, muscular ass in the back. Dean caught himself staring too long. His own boxer briefs had their own tent action going.

  


“Lie on your stomach, Dean. Facing the television,” Cas told him. Wait...was he bottoming? Cas straddled his ass and started massaging Dean’s shoulders. “You said we needed to relax. Would you help me after I help you?”

  


Dean just mumbled his response into the comforter. He hadn’t had a good massage in...what decade was it? Cas’ hands were strong and dug in to work the deep tissue. Years of tension knotted in his back and shoulders came undone. He should have asked Cas to do this years ago. It would only take one healing touch but the process was so much more satisfying. “If you want your turn, I better do it before you put me to sleep.”

  


“All right, Dean.” Cas switched their positions. He’d never had a massage before. He supposed he’d never noticed just how much tension his body held when he wasn’t human. Dean’s fingers digging into his muscles was slightly painful at first, then pleasurable. He didn’t require sleep but he soon understood where Dean had been coming from. Once he was relaxed he was in a bit of a drowsy state. He had to force himself to turn over.

  


With all the exposed skin between them they couldn’t help the roaming hands. Dean traced over the defined muscles and lines with his fingertips. This hot body beneath him was all his to explore. Every curiosity he’d had of Cas he could discover. Where he liked to be touched, what made him shiver. It was slow and sweet between them. New lovers learning each other’s bodies.

  


Dean learned for the first time that Cas was ticklish. A light touch to his lower back and behind his knees made him squirm and laugh. The way he tossed his head back made Dean want to kiss all along his neck and jaw. The sounds Cas made encouraged him to go further, seeking more skin with his lips and tongue. He next found Cas’ nipples to be extremely sensitive. He stores that piece of information for future reference.

  


“Dean...I’m very...aroused. If you don’t feel ready, perhaps we should stop.”

  


“I don’t wanna stop, Cas.” Dean placed his hand on Cas’ hip and hooked his thumb into the waistband of the boyshorts. He kissed his way down Cas’ stomach while fumbling through the plastic bag on the bed. He was relying on feel for the flavored lube. “Is it okay for me to do this?”

  


Cas ran his hand through Dean's hair. “My body I willingly share with you.” He smiled down at Dean. Dean broke the safety seal on the bottle and tugged at Cas’ underwear. Cas lifted his hips to assist him, freeing a quite impressive dick.

  


Dean had fantasized about this. If he’d stayed longer at Sonny’s he probably would have found himself going down on Connie. He’d pictured himself kneeling before Cas with him pressed back against the wall, fingers curled in his hair. Sometimes he imagined it was Cas when some woman he’d picked up was blowing him in the back of the car. Dean had to palm down his own erection before drizzling the cherry lube on Cas.

  


It was hot and heavy on his tongue. Dean lapped at the sweet syrup on the head. He felt it twitch in his mouth. He tried to take on the considerable length but he wasn’t built for deepthroating. He had to work the rest of the shaft with his hand when he bobbed his head. He tried to remember to use his tongue and avoid scraping the sensitive skin with his teeth.

  


Cas’ hips shifted a little then he propped himself up on his elbow to watch. The warmth and wetness of Dean’s mouth on him reminded him of sex. Dean’s plump lips stretched around his cock as he used a hand on Dean’s cheek to guide him. He felt closer to orgasm the faster Dean went. “I’m going to...to... _ come _ , Dean,” he panted with shorter breath.

  


Dean wasn’t sure if he could handle swallowing a load so he popped off to finish Cas by hand. There was still enough slick from the lube for him to glide without too much friction. He watched as Cas’ body tensed. The chords in his neck stood out as he gasped for air he didn’t need. His lips were parted and all the sounds he could make were moans. Dean went a little faster until Cas cried out, pumping cum up onto his own stomach. Dean slowed down to gently milk the rest from the shaft before letting him go.

  


“Dean, that was...I can’t think...no words…”

  


“I’ll take that as a compliment, considering that’s the first time I’ve done that.” Dean smiled. He was temporarily distracted from his own needs by the wrecked and sated look on Cas’ face.

  


“I want you to f-fuck me,” Cas said without looking at him.

  


“Cas, we don’t have to. I can jerk myself off while you watch. Seeing you like this...almost jizzed in my undies, man.”

  


“Dean, I thought about this on the drive. I’m an angel. You can’t hurt me. In fact, you may have to be rougher with me than we anticipated.”

  


“Babe, I thought we were gonna...make love?”

  


“We’ve established loving one another. You’ve just been with me in an extremely intimate way. I’m not saying I don’t want you to take the same care with me that you would with a human. I’m just saying...don’t hold back. I’m a man. I want you to take me like one.”

  


“Fuck. Okay saying stuff like that is getting me hard enough to pound nails. I don’t wanna ruin the party before it gets started.”

  


Cas sat up and wrapped his legs around Dean’s waist. He pulled him into an open kiss, tasting the cherry flavor on his lips. He used Dean’s neck for leverage to pull himself up into his lap. His own cock was spent but he still enjoyed the thrill of how hard Dean felt against him. He retrieved the water based lube and pressed it into Dean’s hand. “I’m feeling very relaxed.”

  


Dean almost choked on his own saliva. He cleared his throat. “T-the website said I gotta open you up first or it might...tear.” He blindly opened the bottle behind Cas’ back. He managed to squirt just a tad too much liquid but it was better than not enough. He pressed his finger to Cas’ hole, hoping it would be similar to fingering a woman. It wasn’t.

  


Cas was relaxed enough for it to slip past his rim. It was so tight in there. And silky smooth. Cas held onto his neck and rocked up and down on the single digit. He showed no sign of any discomfort. Dean teased another finger at the entrance before attempting to breach Cas with both. Cas took him with a heavy moan.

  


Dean wondered if he could find Cas’ prostate like that so he twisted his wrist and pressed his fingertips against Cas’ inner walls. He heard Cas yelp and clench around him. “That was  _ very _ pleasurable,” he announced. His cock twitched and started to fill again. Dean pushed again and Cas’ thighs trembled against him.

  


“I should do one more. Make sure you can take me.” Dean’s fingers were still slippery but he still added more lube before giving Cas three fingers. He could feel the difference from when he started but the muscles were still tighter than anything Dean had felt before. Cas moved with him to fuck himself on Dean’s fingers until he was almost as hard as before. Based on how good it seemed to be for Cas, Dean was no longer afraid to try bottoming.

  


He carefully withdrew his fingers, eliciting a growl of discontent from Cas. Dean just kissed the pout away before easing Cas down on his back like before. He read that the first time would be easier from behind but he just had to see Cas’ face. He got a condom from the box and slipped off his underwear to get ready. Another healthy squeeze of lube on it and he was ready to attempt entry.

  


Cas drew up his knees to give Dean better access. He lined up the tip but slid around Cas’ crack a few times before catching the rim. He eased the head in slowly, trying to get past the tight ring of muscle. Once his head was enveloped, he slid further by mere fractions. It allowed Cas to open up to accept his girth. Dean felt little flutters of muscle contractions and bit his bottom lip to keep from losing himself to the sensations.

  


Cas was patient with him. He just held Dean’s gaze until he was fully sheathed. Dean paused more for himself than Cas’ comfort at that point. “You aren’t hurting me, Dean,” Cas reassured him. “Please.”

  


Dean eased back just a little and pushed back in. Cas felt incredible. He continued with shallow thrusts before lowering his weight down. Cas clung to him like an octopus. Dean kept it slow but also enjoyed being able to bury himself so deep. He’d encountered more than a few women who loved his thickness but couldn’t handle the length. Cas took him all in and still pulled for more.

  


“I’m not something you can break, Dean. You can be harder.”

  


So when Dean pulled back enough to only leave in the tip, he slammed back in, slapping his balls against Cas’ perineum. Cas arched his back and practically screamed, “Yes!” Dean was always eager to please his lovers so he did it Cas’ way, drilling into him hard.

  


“Yes! Dean, just like that! Fuck me. Fuck me till I come again.”

  


Dean felt nails scrape his back. Cas had his head thrown back and was alternating between grunting and moaning. Dean was grinding his teeth in his jaw to postpone his own orgasm. He wanted to see Cas come for him. He rolled them over without pulling out and gripped Cas’ hips to thrust up into him. 

  


Cas had to use Dean’s knees to keep his balance. He slammed himself down to meet every drive up. Dean was hitting that spot again inside him that he found with his fingers. His dick was hard and hitting his stomach. On instinct alone he gripped himself and tried to pump his shaft in time with the thrusts. His ears were ringing and his vision doubled. Cas’ eyes rolled back in his head as cum landed on he and Dean both.

  


Dean could have come from the sight alone but the hard clench on his cock just squeezed his orgasm from him. His grip on Cas was enough to bruise another human as he held Cas down on him to ride it out. “I don’t think I’ve ever come that hard in my life.”

  


Cas stayed seated on him for the few minutes it took to come down from the endorphin rush. He disliked the feel of Dean exiting his body but otherwise he was extremely satisfied with their coupling. He used a bit of grace to clean them both up before curling into Dean's side. “I believe we just proved that fucking and making love are not mutually exclusive.”

  


“Ya think?” Dean replied. “I was gonna go all rom-com and you were like this insatiable beast. Damn, Cas. You definitely ruined me.”

  


“Ruined you?” Cas made small circles on Dean’s chest with his fingers.

  


“Yeah. Like ruined me for anybody else. Meaning the only person I wanna ever have sex with again is you.”

  


“Then I concur. I seem to be ruined as well.” Cas threw his leg over Dean’s. “I’d like you to experience what I felt.”

  


“You mean bottoming? Looked like you were enjoying the hell out of it. I’m up for trying it sometime. Can’t guarantee I’ll want you to pound  _ me _ like that. But yeah. We’ll get around to all kinds of ways to please each other.”

  


Cas kissed his cheek before helping remove the condom and gathering the lube bottles. He eyed the unopened one. “Dean? This one is waterproof. How complicated is shower sex?”

  


“You’re killing me, Cas. Us humans don’t have the kind of refractory period you obviously do. Maybe we should finish our leftovers and hit the sack. We can revisit the shower sex idea in the morning.”

  


Cas grinned at him. “Perhaps I’ll close my eyes and meditate for awhile when you’re sleeping. Sex is exhilarating but exhausting.”

  


“Only when you do it right, Sunshine.”

  


***

  


They went back to the same diner for breakfast the next morning. Dean and Cas were all smiles and stolen glances. Sam pretended to puke a couple times but he was happy for them. He’d found another school to look into that seemed pretty progressive.

  


“Agent Bonham? I didn’t know you knew the Winchesters.”

  


All three men looked towards the voice. Sam didn’t recognize him. Dean stood to greet him.

  


“Hey, Connie. Small world, huh? He’s an old college buddy of Cas’. I guess an FBI agent is expected after the recent tragedy.”

  


Sam still looked confused. “Oh! You’re the principal of the high school. I was supposed to interview you but I think I got everything from the sheriff.”

  


“She stopped by. I recognized you from her description. I have time later today…” Connie offered. 

  


“Actually I have to head out after breakfast. I have a lead on our unsub. I can’t divulge anything but...I’m hoping we bring Ashley’s killer to justice.” Sam played into his role.

  


“That’s all any of us hope for, Agent. Dean, Cas, nice to see you again before you left. I have a to go order waiting for me and a faculty meeting. Hope to hear from you soon about Jack.” Connie shook their hands and left for the counter.

  


Sam smirked. “Wow. Your first boyfriend.”

  


Dean put his arm around Cas. “And this devastatingly handsome guy is my last.”

  


Sam’s phone vibrated. He took it out and checked the message and attachment. He turned the screen to Dean and Cas. They both scrunched their faces. “Ketch shouldn't have pissed off Rowena,” Sam commented. “Looks like we can start heading home.”

  


“Home is where the memory foam is, Sam.”

  


“Your bed is quite comfortable, Dean,” Cas chimed in. 

  


“Thought you guys  _ just _ got together.” Sam raised an eyebrow.

  


Dean shot Sam one of his own bitchfaces. “Netflix without the chill, Bitch.”

  


“Whatever, Jerk. At least I won’t have to block out the sound of mattress springs squeaking.” Sam pushed his plate away and gulped down the rest of his tepid coffee. “Should we send Rowena a fruit basket or something?” He asked as he shrugged his jacket on. 

  


“A fruit basket? Dude, you owe her a lapdance for taking out Ketch,” Dean teased. “We’ll max a scam card and send her some top shelf scotch.” He put his hand low on Cas’ back, under the trenchcoat. Everything between them was more intimate now, including the brush of Cas’ hands on his shoulder. “Hey, Sam? You mind giving up shotgun for Cas?”

  


Sam patted Cas’ shoulder. “Sure. I’ll just sprawl out in the back so Pumpkin and Hunny Bunny can hold hands like like a couple teenagers.”

  


It was a long ride of relentless teasing and kissy noises.


End file.
